Adventures In Forced Cross Dressing

lion in purple thong

Front view of purple thong. I don’t want all our posts to show panty pictures, but this pair is incredibly comfortable to wear and very embarrassing to see on my body. From Mrs. Lion’s perspective, it’s perfection. [Click image to enlarge]

Yesterday morning, Mrs. Lion put a purple thong on the bed for me to wear. It was frilly like the one I showed the other day. I dutifully put it on and continued dressing. Actually, I looked at myself in the mirror first. Ridiculous! I was working at home but had a number of video conferences, so I got completely dressed. To my surprise, that silly thong was more comfortable than my boy underwear. It stayed up (most of my underwear tends to ride down) and felt great against my penis. Mrs. Lion has left me wild since we went on vacation.

I’ve read that some other guys like the way women’s underwear feels. My experience so far ranges from uncomfortable to acceptable. I’ve always been very happy to return to my Calvin Klein red boxer briefs. This time, I’m not so sure. For some reason, this thong stays up even when I am not wearing anything else. The front comfortably accommodates my genitals and the rear string sits comfortably as well. I won’t comment on the style. I like this thong much better when it is covered by pants. I’m definitely not a cross dresser. But, what can I say? This thong feels great.

Lion's butt with thong

Here is a rear view of the purple thong. I can’t really feel the string going through my crack. [Click image to enlarge]

For the record, I have some male thongs from Obviously. They are fine and fit well. But they do ride down in the back sometimes and the front is not as comfortable as this purple thong. Weird.

Anyway, I’m sure you are getting bored with my underwear adventures. Mrs. Lion has done a great job finding humiliating things for me to wear. Last night she had me model a lace bra. This number looked totally silly on me. There is no way I can rationalize wearing it. It is female-only underwear. Wearing a bra is way more embarrassing than wearing frilly panties.

She also had me try on — get this — a rosebud baby doll set that included a top that came down just below my belly button and a thong in a matching pattern. You can see it here. It looks a thousand times better on the model than it does on me. Holy shit! There are still a scary pile of undies I haven’t modeled yet.

Mrs. Lion is working out how she will integrate forced cross dressing into our daily lives. In the short time we have been doing it, she either lays out a panty or tells me to wear my regular male underwear. I’ve only worn the bra for a few seconds.

There’s no question that I’m embarrassed wearing this stuff. I think that Mrs. Lion is enjoying the shopping and perhaps is thinking of ways to use forced cross dressing to further humiliate me. It’s all harmless fun for her. I like the way having her make me wear things makes me feel.

More interesting, she seems to enjoy this. She’s having fun shopping for me and appears to get a kick out of seeing me wearing frilly things. She frowns when she doesn’t think the item works well for me; like the baby doll camisole. I think she is genuinely interested in creating a feminine wardrobe for me. I know for a fact that she is having more fun than I.

Caged male half of a happy couple practicing enforced male chastity and domestic discipline. Locked since 1/2014. Domestic discipline 3/2015. Lion’s first mouth soaping was 7/17.

6 comments on “Adventures In Forced Cross Dressing
  1. I have always had a fascination for forced feminization, and started crossdressing at a young age, so I’ve found it really interesting to explore the situation from your perspective. Thanks for continuing to share!

  2. Jim says:

    Perhaps You need to change Your Blog name from Male Chastity Journal to Female Led sissy transformation Journal.

    • Caged Lion says:

      Isn’t your comment special. There’s always one in every bunch.

      • trappedandloved says:

        Jim has a point. But seriously do you think you have now found your true kink rather than male chastity?

        I remember that Tom Allen had a post a while back complaining about the number of what he thought were fantasy blogs linking male chastity with sissification. Perhaps there is a strong link between the two?

        Or perhaps is this a side show to try and feel control? A proxy for a need to be controlled? It seems your experience of chastity has involved very little enforced denial and so are you seeking a feeling of being controlled in other ways?

        This led me to think about one of your earlier notes in which you suggested that people could become addicted to denial and want longer and longer waits. I think you are right. I think all of these things release dopamine in the brain and and are at least mildly addictive. But so what? If the consequence of the addiction is a happy marriage does it matter?

        • Caged Lion says:

          I think in my case it is a matter of feeling a little humiliated at the hands of Mrs. Lion. It’s about control. I will never go for sissification. Nuh uh! I think that it’s exactly what you say. I don’t need to cross dress. I don’t want to do it. But, I can see a relationship between virtually removing the penis and the desire to be female. A chastity device is certainly a symbolic way to do that.

What do you think?